Novel Adenosine and 1,n6-Ethenoadenosine Derivatives for Cancer Treatment

Patent Abstract

The invention concerns adenosine derivatives of Formula I, or pharmaceutically acceptable salts thereof:wherein: R1 is absent, the bond between N1 and C6 is a double bond, the bond between C6 and the exocyclic amino nitrogen is a single bond, and R2 and R3 are each H, or R1 and R2 together form an ethenylene group, the bond between N1 and C6 is a single bond, the bond between C6 and the exocyclic amino nitrogen is a double bond, and R3 is absent; and R4 and R5 are each independently each a linear or branched C1-C16-alkyl group, provided that R4 and R5 together comprise 11 to 17 carbon atoms, or R4 and R5 together with the carbon atom to which they are bound form a monocyclic or polycyclic cycloaliphatic ring with 10 to 15 carbon atoms.The compounds of Formula I have cancerostatic and cancerotoxic activity.

Simple SummaryContent extracted from patent full text and abstract with AI.

This patent covers a new class of adenosine and 1,N6-ethenoadenosine derivatives specifically designed for cancer treatment. These compounds, with particular modifications at defined chemical positions, demonstrate strong cancer-inhibiting (cancerostatic) and cancer-killing (cancerotoxic) effects against a variety of tumor cell lines, including brain tumors, colon, liver, kidney, and pancreatic cancers. Notably, these derivatives show higher efficacy than standard chemotherapeutic drugs like temozolomide (TMZ), 5-fluorouracil (5-FU), and even gemcitabine for pancreatic cancers, potentially offering improved cancer therapies with reduced side effects.

Use CasesContent extracted from patent full text and abstract with AI.

• Chemotherapeutic treatment for brain tumors such as gliomas and glioblastomas.
• Treatment of colon adenocarcinoma.
• Therapy for hepatocellular (liver) carcinoma.
• Treatment of renal carcinoma (kidney cancer).
• Chemotherapy for pancreatic cancer and pancreatic ductal adenocarcinoma.
• Development of new anti-cancer pharmaceutical compositions for injectable or parenteral administration.
• Use as diagnostic or research probes due to fluorescent properties in some compound variants.
• Use in studying cellular and enzymatic mechanisms in cancer research.

BenefitsContent extracted from patent full text and abstract with AI.

• Demonstrated higher efficacy in vitro compared to current standard drugs (TMZ, 5-FU, gemcitabine), including at lower effective concentrations.
• Active against a wide range of solid tumors, making them suitable for multiple cancer types.
• Likely to cause fewer side effects, thanks to improved therapeutic index (better ratio of therapeutic effect to toxicity).
• Improved membrane permeability and cellular uptake due to optimized molecular weight, number of hydrogen bridge donors/acceptors, and lipophilicity (logPOW).
• Some derivatives have fluorescent properties, allowing for easy detection in biological samples and use in diagnostics or mechanism-of-action studies.
• Available in forms suitable for pharmaceutical formulation, such as dry powder for reconstitution, enabling flexibility in clinical use.
• Potential to achieve complete cytotoxicity (cell death) where standard drugs could not, providing promise for treatment-resistant cancers.

Technical Classifications (CPCs)

Inventors & Applicants